“I’m Peggy by name and Peggy by nature,” the dominatrix said as she bent him over. Darren looked up at the sexy yet terrifying woman who towered over him in her thigh-high leather boots. How on earth had his bachelor party stag night ended up like this? And was he really going to submit and let her do that to him?

When burly tradesman Tyler finds some women’s clothes hidden away at the empty school he’s working on, he can’t resist exploring his secret sissy fantasies. But the strict Headmistress catches him in the act and punishes him in a most unexpected way–forced to fully feminize, he is spanked over her desk and made to satisfy both her and himself. But who’s enjoying it more–the hot but stern Headmistress, or big, butch Tyler, all dressed up as a girl?

When Connor starts a new job, he's pleased to find he's the only male in an office full of attractive women. But then he starts getting mysterious, anonymous messages telling him to do some very taboo things. Intrigued, he follows the instructions....

Dave is at the end of his rope with Robin, his long-term girlfriend. She’s become toxic: jealous, mean, untrusting—and she’s even started to stalk Dave whenever he goes out. When Dave meets Sandra, he decides to make a clean break with Robin, and Robin doesn’t take the breakup lightly. She’s convinced that Dave had been cheating on her, and she’s determined to make him pay for his unfaithfulness. Just as Dave’s new relationship starts getting serious, Robin unleashes her plot of humiliation and reluctant feminization on her ex, and Dave has to play along if he wants to remain with his new boo.

The mystery of the femdom office continues as Connor is trained as the submissive, sissified office toy. Under her desk, Connor must show his absolute devotion to his demanding Mistress and the other women, as they torment and use him at work. To keep him in line, his dominant Mistress places him in male chastity, further controlling him with tease and denial and ensuring that he can only find satisfaction at her command.

Ricki has the perfect life: a beautiful house, a beautiful fiancée, and the easiest job in the world. By day-trading from home, he earns six-figures with just a few hours of work each day. At least he did, until he wakes up to see that his trading account has been shut down.

Prom is approaching, and Jeremy has his eye on Amanda. Well, every guy has his eye on Amanda, and a few of the girls too. She’s the hottest girl in school, so Jeremy doesn’t actually think he has a shot.

Kenny has a bully problem: a bad bully problem. Every day is torment, until a new girl arrives at the school. Alex is tall, athletic, and beautiful—and she doesn’t take crap from anyone. When she sees Kenny being targeted by the school’s meanest bullies, she puts her foot down—right into the face of the meanest of them all. And just like that, the bad boys are too afraid to pester Kenny. Now, school life for Kenny isn’t looking so grim. It seems like he’s in the clear, until Alex reveals to him that there is something she wants from the young, petite-framed man.

Toni’s twin brother Riley has just graduated from art school, and Toni invites Riley to live with her in California until he can find a good job. Toni has always wanted a sister, and Riley has always been a bit of a femboy anyway, so Toni puts her plan into action. She manages to enlighten Riley about the nuances of presenting his feminine side and immerses him in the pleasures of catering to his feminine persona.

At the Sissy Dollhouse men are captured by the beautiful dominatrix Tanya and turned into mind controlled transgender dolls using seduction, drugs, hypnosis, surgery, and hormones; then they are used as programmable prostitutes for fulfilling the fantasies of rich clients.